Cork taint of wines: the formation, analysis, and control of 2,4,6- trichloroanisole

Abstract

Cork taint has devastating effects on the aroma and quality of the wine, which can cause an annual loss of may be up to more than one billion dollars. There are many causes of cork taint, but 2,4,6-trichloroanisole (2,4,6-TCA) is a major contributor, giving the wine a wet-moldy smell. This study provided a comprehensive overview of the occurrence, detection, and control/remediation of 2,4,6-TCA. The occurrence and formation mechanisms of 2,4,6-TCA mainly include microbial O-methylation of chlorophenols and chlorination of anisole. The source of 2,4,6-TCA in wine is the cork or other woodworks, but it is also possible to contaminate wine from the environment. Due to the extremely low odor threshold concentration of 2,4,6-TCA, the effective sample pre-enrichment for instrument identification and quantification is more important. The control/remediation strategies of 2,4,6-TCA mainly include eliminating 2,4,6-TCA in cork and removing 2,4,6-TCA from wine by adsorption. Finally, the challenges and possible future research directions in this research field were discussed and proposed.

Keywords

Wine / 2,4,6-trichloroanisole / Cork taint / Analysis methods / Remediation methods

References

[1] Peña-Neira A, Fernández de Simón B, García-Vallejo MC, Hernández T, Cadahía E, et al. Presence of cork-taint responsible compounds in wines and their cork stoppers European Food Research and Technology. 2000, 211, 257-61

[2] Keng A, Botezatu A. Uncorking haloanisoles in wine Molecules. 2023, 28, 2532

[3] Jové P, Pareras A, De Nadal R, Verdum M. Development and optimization of a quantitative analysis of main odorants causing off flavours in cork stoppers using headspace solid-phase microextraction gas chromatography tandem mass spectrometry Journal of Mass Spectrometry. 2021, 56, e4728

[4] Dietrich AM, Burlingame GA. A review: The challenge, consensus, and confusion of describing odors and tastes in drinking water Science of The Total Environment. 2020, 713, 135061

[5] Judet-Correia D, Bensoussan M, Charpentier C, Dantigny P. Influence of temperature, copper and CO ₂ on spore counts and geosmin production by Penicillium expansum Australian Journal of Grape and Wine Research. 2013, 19, 81-86

[6] Romano A, Navarini L, Lonzarich V, Bogialli S, Pastore P, et al. 2,4,6-Trichloroanisole off-flavor screening in green Coffea arabica by a novel vocus NO ⁺ CI-MS method: A study on green coffee from different geographical origins Journal of Agricultural and Food Chemistry. 2022, 70, 11412

[7] Tempere S, Schaaper MH, Cuzange E, de Revel G, Sicard G. Masking of several olfactory notes by infra-threshold concentrations of 2,4,6-trichloroanisole Chemosensory Perception. 2017, 10, 69-80

[8] Takeuchi H, Kato H, Kurahashi T. 2,4,6-Trichloroanisole is a potent suppressor of olfactory signal transduction Proceeding of the National Academy of Sciences of the United States of America. 2013, 110, 16235-40

[9] Abhijith GR, Ostfeld A. Modeling the formation and propagation of 2, 4, 6-trichloroanisole, a dominant taste and odor compound, in Water Distribution Systems Water. 2021, 13, 638

[10] Zhang K, Cao C, Zhou X, Zheng F, Sun Y, et al. Pilot investigation on formation of 2,4,6-trichloroanisole via microbial O-methylation of 2,4,6-trichlorophenol in drinking water distribution system: An insight into microbial mechanism Water Research. 2018, 131, 11-21

[11] Ge F, Zhu L, Chen H. Effects of pH on the chlorination process of phenols in drinking water Journal of Hazardous Materials. 2006, 133, 99-105

[12] Zhang K, Zhou X, Zhang T, Mao M, Li L, et al. Kinetics and mechanisms of formation of earthy and musty odor compounds: Chloroanisoles during water chlorination Chemosphere. 2016, 163, 366-72

[13] Zhang K, Luo Z, Zhang T, Mao M, Fu J. Study on formation of 2,4,6-trichloroanisole by microbial O-methylation of 2,4,6-trichlorophenol in lake water Environmental Pollution. 2016, 219, 228-34

[14] Ghochlavi N, Aghapour AA, Khorsandi H. Biodegradation of 2,4,6 trichlorophenol by sequencing batch reactors (SBR) equipped with a rotating biological bed and operated in an anaerobic-aerobic condition Frontiers in Environmental Science. 2022, 10, 2053

[15] Zheng W, Su R, Lin X, Liu J. Nanochannel array modified three-dimensional graphene electrode for sensitive electrochemical detection of 2,4,6-trichlorophenol and prochloraz Frontiers in Chemistry. 2022, 10, 954802

[16] Li H, Li J, Hou C, Du S, Ren Y, et al. A sub-nanomole level electrochemical method for determination of prochloraz and its metabolites based on medical stone doped disposable electrode Talanta. 2010, 83, 591-95

[17] Huff J. Long-term toxicology and carcinogenicity of 2,4,6-trichlorophenol Chemosphere. 2012, 89, 521-25

[18] Tian F, Qiao C, Wang C, Pang T, Guo L, et al. Dissipation behavior of prochloraz and its metabolites in grape under open-field, storage and the wine-making process Journal of Food Composition and Analysis. 2022, 114, 104846

[19] Prak S, Gunata Z, Guiraud JP, Schorr-Galindo S. Fungal strains isolated from cork stoppers and the formation of 2,4,6-trichloroanisole involved in the cork taint of wine Food Microbiology. 2007, 24, 271-80

[20] Maggi L, Mazzoleni V, Fumi MD, Salinas MR. Transformation ability of fungi isolated from cork and grape to produce 2,4,6-trichloroanisole from 2,4,6-trichlorophenol Food Additives & Contaminants: Part A. 2008, 25, 265-69

[21] Alvarez-Rodríguez ML, López-Ocaña L, López-Coronado JM, Rodríguez E, Martínez MJ, et al. Cork taint of wines: role of the filamentous fungi isolated from cork in the formation of 2,4,6-trichloroanisole by O-methylation of 2,4,6-trichlorophenol Applied and Environmental Microbiology. 2002, 68, 5860-69

[22] Álvarez-Rodríguez ML, Belloch C, Villa M, Uruburu F, Larriba G, et al. Degradation of vanillic acid and production of guaiacol by microorganisms isolated from cork samples FEMS Microbiology Letters. 2003, 220, 49-55

[23] Endo M, Matsui C, Maeta N, Uehara Y, Matsuda R, et al. Growth characteristics of Aspergillus oryzae in the presence of 2,4,6-trichlorophenol The Journal of General and Applied Microbiology. 2021, 67, 256-59

[24] Nyström A, Grimvall A, Krantz-Rüilcker C, Sävenhed R, Åkerstrand K. Drinking water off-flavour caused by 2,4,6-trichloroanisole Water Science and Technology. 1992, 25, 241-49

[25] Zhou X, Zhang K, Zhang T, Yang Y, Ye M, et al. Formation of odorant haloanisoles and variation of microorganisms during microbial O-methylation in annular reactors equipped with different coupon materials Science of the Total Environment. 2019, 679, 1-11

[26] Zhou X, Zhang K, Zhang T, Cen C, Pan R. Biotransformation of halophenols into earthy-musty haloanisoles: Investigation of dominant bacterial contributors in drinking water distribution systems Journal of Hazardous Materials. 2021, 403, 123693

[27] Bai X, Zhang T, Qu Z, Li H, Yang Z. Contribution of filamentous fungi to the musty odorant 2,4,6-trichloroanisole in water supply reservoirs and associated drinking water treatment plants Chemosphere. 2017, 182, 223-30

[28] Zheng T, Ma YL, Li WS, Deng JX, Li H, et al. Trichoderma species from rhizosphere of Oxalis corymbose release volatile organic compounds inhibiting the seed germination and growth of Echinochloa colona Arabian Journal of Chemistry. 2023, 16, 105274

[29] Hitfield FB, Ly Nguyen TH, Tindale CR. Effect of relative humidity and incubation time on the O-methylation of chlorophenols in fibreboard by Paecilomyces variotii Journal of the Science of Food and Agriculture. 1991, 55, 19-26

[30] Gee JM, Peel JL. Metabolism of 2,3,4,6 tetrachlorophenol by microorganisms from broiler house litter Journal of General Microbiology. 1974, 85, 237-43

[31] Coque JJR, Alvarez-Rodríguez ML, Larriba G. Characterization of an inducible chlorophenol O-methyltransferase from Trichoderma longibrachiatum involved in the formation of chloroanisoles and determination of its role in cork taint of wines Applied and Environmental Microbiolog. 2003, 69, 5089-95

[32] Prat C, Ruiz-Rueda O, Trias R, Anticó E, Capone D, et al. Molecular fingerprinting by PCR-denaturing gradient gel electrophoresis reveals differences in the levels of microbial diversity for musty-earthy tainted corks Applied and Environmental Microbiology. 2009, 75, 1922-1931

[33] Tang Y, Wu Z, Zhang Y, Wang C, Ma X, et al. Cultivation-dependent and cultivation-independent investigation of O-methylated pollutant-producing bacteria in three drinking water treatment plants Water Research. 2023, 231, 119618

[34] Allard AS, Remberger M, Neilson AH. Bacterial O-methylation of halogen-substituted phenols Applied and Environmental Microbiology. 1987, 53, 839-45

[35] Azevedo J, Brandao E, Soares S, Oliveira J, Lopes P, et al. Polyphenolic characterization of nebbiolo red wines and their interaction with salivary proteins Foods. 2020, 9, 1867

[36] Azevedo J, Jesus M, Brandao E, Soares S, Oliveira J, et al. Interaction between salivary proteins and cork phenolic compounds able to migrate to wine model solutions Food Chemistry. 2022, 367, 130607

[37] Azevedo J, Lopes P, Mateus N, de Freitas V. Cork, a natural choice to wine? Foods. 2022, 11, 2638

[38] Monteiro S, Bundaleski N, Malheiro A, Cabral M, Teodoro OMND. Cross contamination of 2, 4, 6-trichloroanisole in cork stoppers Journal of Agricultural and Food Chemistry. 2022, 70, 6747-54

[39] Rebezov M, Saeed K, Khaliq A, Rahman SJU, Sameed N, et al. Application of electrolyzed water in the food industry: A review Applied Sciences-Basel. 2022, 12, 6639

[40] Zhang WL, Cao JK, Jiang WB. Application of electrolyzed water in postharvest fruits and vegetables storage: A review Trends in Food Science & Technology. 2021, 114, 599-607

[41] Cravero F, Englezos V, Rantsiou K, Torchio F, Giacosa S, et al. Control of Brettanomyces bruxellensis on wine grapes by post-harvest treatments with electrolyzed water, ozonated water and gaseous ozone Innovative Food Science & Emerging Technologies. 2018, 47, 309-16

[42] Giacosa S, Gabrielli M, Torchio F, Río Segade S, Grobas AMM, et al. Relationships among electrolyzed water postharvest treatments on winegrapes and chloroanisoles occurrence in wine Food Research International. 2019, 120, 235-43

[43] Gabrielli M, Englezos V, Rolle L, Río Segade S, Giacosa S, et al. Chloroanisoles occurrence in wine from grapes subjected to electrolyzed water treatments in the vineyard Food Research International. 2020, 137, 109704

[44] Tarasov A, Jung RE. Is Airborne 2,4,6-Trichloroanisole (TCA) a threat for bottled wine? Australian Journal of Grape and Wine Research. 2023, 2023, 6637804

[45] Romano A, Capozzi V, Khomenko I, Biasioli F. Advances in the Application of Direct Injection Mass Spectrometry Techniques to the Analysis of Grape, Wine and Other Alcoholic Beverages Molecules. 2023, 28, 7642

[46] Zhang J, Zhang A, Fan C, Li X, Cui Z, et al. Determination of multihalo- phenols and anisoles in wine by gas chromatography tandem mass spectrometry through online derivatization and head space solid phase Microextraction Food Analytical Methods. 2022, 15, 3435-43

[47] Ruiz-Delgado A, Arrebola-Liébanas FJ, Romero-González R, López-Ruiz R, Garrido Frenich A. Headspace solid-phase microextraction coupled to gas chromatography-tandem mass spectrometry for the determination of haloanisoles in sparkling (cava and cider) and non-sparkling (wine) alcoholic beverages Food Additives and Contaminants: Part A. 2016, 33, 1535-44

[48] Özhan D, Anli RE, Vural N, Bayram M. Determination of Chloroanisoles and Chlorophenols in Cork and Wine by using HS-SPME and GC-ECD Detection Journal of the Institute of Brewing. 2009, 115, 71-77

[49] Karpas Z, Guamán AV, Calvo D, Pardo A, Marco S. The potential of ion mobility spectrometry (IMS) for detection of 2,4,6-trichloroanisole (2,4,6-TCA) in wine Talanta. 2012, 93, 200-5

[50] Lichvanová Z, Ilbeigi V, Sabo M, Tabrizchi M, Matejčík S. Using corona discharge-ion mobility spectrometry for detection of 2,4,6-Trichloroanisole Talanta. 2014, 127, 239-43

[51] Márquez-Sillero I, Aguilera-Herrador E, Cárdenas S, Valcárcel M. Determination of 2, 4, 6-tricholoroanisole in water and wine samples by ionic liquid-based single-drop microextraction and ion mobility spectrometry Analytica Chimica Acta. 2011, 702, 199-204

[52] Márquez-Sillero I, Cárdenas S, Valcárcel M. Headspace–multicapillary column–ion mobility spectrometry for the direct analysis of 2,4,6-trichloroanisole in wine and cork samples Journal of Chromatography A. 2012, 1265, 149-54

[53] Jové P, Vives-Mestres M, De Nadal R, Verdum M. Development, optimization and validation of a sustainable and quantifiable methodology for the determination of 2,4,6-trichloroanisole, 2,3,4,6-tetrachloroanisole, 2,4,6-tribromoanisole, pentachloroanisole, 2-methylisoborneole and geosmin in air Processes. 2021, 9, 1571

[55] Santos JP, Sayago I, Sanjurjo JL, Perez-Coello MS, Díaz-Maroto MC. Rapid and non-destructive analysis of corky off-flavors in natural cork stoppers by a wireless and portable electronic nose Sensors. 2022, 22, 4687

[56] Meléndez F, Arroyo P, Gómez-Suárez J, Palomeque-Mangut S, Suárez JI, et al. Portable electronic nose based on digital and analog chemical sensors for 2,4,6-trichloroanisole discrimination Sensors. 2022, 22, 3453

[57] Peres AM, Freitas P, Dias LG, Sousa MEBC, Castro LM, et al. Cyclic voltammetry: A tool to quantify 2,4,6-trichloroanisole in aqueous samples from cork planks boiling industrial process Talanta. 2013, 117, 438-44

[58] Sanvicens N, Sánchez-Baeza F, Marco MP. Immunochemical determination of 2,4,6-trichloroanisole as the responsible agent for the musty odor in foods. 1. Molecular modeling studies for antibody production Journal of Agricultural and Food Chemistry. 2003, 51, 3924-31

[59] Moore E, Pravda M, and Guilbault GG. Development of a biosensor for the quantitative detection of 2, 4, 6-trichloroanisole using screen printed electrodes Analytica Chimica Acta. 2003, 484, 15-24

[60] Lausterer R, Sanvicens N, Marco MP, Hock B. Enzyme immunoassay for 2,4,6-trichloroanisole based on monoclonal antibodies Analytical Letters. 2003, 36, 713-29

[61] Apostolou T, Pascual N, Marco MP, Moschos A, Petropoulos A, et al. Extraction-less, rapid assay for the direct detection of 2,4,6-trichloroanisole (TCA) in cork samples Talanta. 2014, 125, 336-40

[62] Cappellin L, Lopez-Hilfiker FD, Pospisilova V, Ciotti L, Pastore P, et al. Thermal desorption-vocus enables online nondestructive quantification of 2,4,6-trichloroanisole in cork stoppers below the perception threshold Analytical Chemistry. 2020, 92, 9823-29

[63] Damiano C, Intrieri D, Sonzini P, Rizzato S, Di Natale C, et al. Nickel (0) complexes as promising chemosensors for detecting the " cork taint" in wine European Journal of Inorganic Chemistry. 2022, 2022, e202101013

[64] Lizarraga E, Irigoyen A, Belsue V, González-Peñas E. Determination of chloroanisole compounds in red wine by headspace solid-phase microextraction and gas chromatography-mass spectrometry Journal of Chromatography A. 2004, 1052, 145-49

[65] Zalacain A, Alonso GL, Lorenzo C, Iñiguez M, Salinas MR. Stir bar sorptive extraction for the analysis of wine cork taint Journal of Chromatography A. 2004, 1033, 173-178

[66] Campillo N, Viñas P, Cacho JI, Peñalver R, Hernández-Córdoba M. Evaluation of dispersive liquid-liquid microextraction for the simultaneous determination of chlorophenols and haloanisoles in wines and cork stoppers using gas chromatography-mass spectrometry Journal of Chromatography A. 2010, 1217, 7323-30

[67] Bai X, Zhang T, Li H, Yang Z. Simultaneous dispersive liquid–liquid microextraction based on a low-density solvent and derivatization followed by gas chromatography for the simultaneous determination of chloroanisoles and the precursor 2,4,6-trichlorophenol in water samples Journal of Separation Science. 2016, 39, 2146-55

[68] Taylor MK, Young TM, Butzke CE, and Ebeler SE. Supercritical fluid extraction of 2, 4, 6-trichloroanisole from cork stoppers Journal of Agricultural and Food Chemistry. 2000, 48, 2208-11

[69] Ezquerro O, Garrido-López A, Tena MT. Determination of 2,4,6-trichloroanisole and guaiacol in cork stoppers by pressurised fluid extraction and gas chromatography-mass spectrometry Journal of Chromatography A. 2006, 1102, 18-24

[70] Callejón RM, Ubeda C, Ríos-Reina R, Morales, ML, Troncoso AM. Recent developments in the analysis of musty odour compounds in water and wine: A review Journal of Chromatography A. 2016, 1428, 72-85

[71] Dong ZY, Lin YL, Zhang TY, Hu CY, Pan Y, et al. The formation, analysis, and control of chlor(am)ination-derived odor problems: A review Water Research. 2021, 203, 117549

[72] Marsol-Vall A, Ainsa S, Lopez R, Ferreira V. Development and validation of a method for the analysis of halophenols and haloanisoles in cork bark macerates by stir bar sorptive extraction heart-cutting two-dimensional gas chromatography negative chemical ionization mass spectrometry Journal of Chromatography A. 2022, 1673, 463186

[73] Pizarro C, Sáenz-González C, Pérez-del-Notario N, González-Sáiz JM. Development of a dispersive liquid–liquid microextraction method for the simultaneous determination of the main compounds causing cork taint and Brett character in wines using gas chromatography–tandem mass spectrometry Journal of Chromatography A. 2011, 1218, 1576-84

[74] Goto S, Urase T, and Nakakura K. Novel and simple method for quantification of 2, 4, 6-trichlorophenol with microbial conversion to 2,4,6-trichloroanisole Microorganisms. 2023, 11, 2133

[75] Wang C, Zou P, Zhang T, Li H, Yang Z. Simultaneous determination of haloanisoles and halophenols in water using in situ acylation combined with solid-phase microextraction with gas chromatography and mass spectrometry Journal of Separation Science. 2017, 40, 514-23

[76] Stranig S, Leitner E, Leis D, Siegmund B. Mouldy and musty off-flavour in garlic is caused by the presence of 2,4,6-trichloroanisole Journal of Food Composition and Analysis. 2024, 126, 105936

[77] Zhang N, Xu B, Qi F, Kumirska J. The occurrence of haloanisoles as an emerging odorant in municipal tap water of typical cities in China Water Research. 2016, 98, 242-49

[78] Vakinti M, Mela SM, Fernández E, Psillakis E. Room temperature and sensitive determination of haloanisoles in wine using vacuum-assisted headspace solid-phase microextraction Journal of Chromatography A. 2019, 1602, 142-49

[79] González-Centeno MR, Tempère S, Teissedre PL, Chira K. Use of alimentary film for selective sorption of haloanisoles from contaminated red wine Food Chemistry. 2021, 350, 128364

[80] Alañón ME, Alarcón M, Díaz-Maroto IJ, Pérez-Coello MS, Díaz-Maroto MC. Corky off-flavor compounds in cork planks at different storage times before processing. Influence on the quality of the final stoppers Journal of the Science of Food Agriculture. 2021, 101, 4735-42

[81] Cacho JI, Nicolás J, Viñas P, Campillo N, Hernández-Córdoba M. Control of halophenol and haloanisole concentration in wine cellar environments, wines, corks and wood staves using gas chromatography with mass spectrometry Australian Journal of Grape and Wine Research. 2016, 22, 391-98

[82] Cacho JI, Nicolás J, Viñas P, Campillo N, Hernández-Córdoba M. Direct sample introduction-gas chromatography-mass spectrometry for the determination of haloanisole compounds in cork stoppers Journal of Chromatography A. 2016, 1475, 74-79

[83] Valdés O, Marican A, Avila-Salas F, Castro RI, Mirabal Y, et al. Simple approach for cleaning up 2,4,6-trichloroanisole from alcoholic-beverage-reconstituted solutions using polymeric materials Australian Journal of Grape and Wine Research. 2019, 25, 327-37

[84] Cosme F, Gomes S, Vilela A, Filipe-Ribeiro L, Nunes FM. Air-depleted and solvent-impregnated cork powder as a new natural and sustainable fining agent for removal of 2, 4, 6-trichloroanisole (TCA) from red wines Molecules. 2022, 27, 4614

[85] Garde-Cerdán T, Zalacain A, Lorenzo C, Alonso JL, Salinas MR. Molecularly imprinted polymer-assisted simple clean-up of 2,4,6-trichloroanisole and ethylphenols from aged red wines American Journal of Enology and Viticulture. 2008, 59, 396-400

[86] Philipp C, Sari S, Brandes W, Nauer S, Patzl-Fischerleitner E, et al. Reduction in off-flavors in wine using special filter layers with integrated zeolites and the effect on the volatile profile of Austrian wines Applied Sciences. 2022, 12, 4343

[87] Guedes P, Mateus EP, Fernandes JP, Ribeiro AB. Electro-technologies for the removal of 2, 4, 6-trichloroanisole from naturally contaminated cork discs: Reactor design and proof of concept Chemical Engineering Journal. 2019, 361, 80-88

[88] Recio E, Álvarez-Rodríguez ML, Rumbero A, Garzón E, Coque JJR. Destruction of chloroanisoles by using a hydrogen peroxide activated method and its application to remove chloroanisoles from cork stoppers Journal of Agricultural and Food Chemistry. 2011, 59, 12589-97

[89] Vlachos P, Stathatos E, Lyberatos G, Lianos P. Gas-phase photocatalytic degradation of 2,4,6-trichloroanisole in the presence of a nanocrystalline Titania film. Applications to the treatment of cork stoppers Catalysis Communications. 2008, 9, 1987-90

[90] Sainz-García A, González-Marcos A, Múgica-Vidal R, Muro-Fraguas I, Gallarta-González F, et al. Wine corks decontamination using plasma activated water Current Research in Food Science. 2023, 7, 100639

[91] Fang L, Hallam D, Bermúdez R. Experimental studies on removal of airborne haloanisoles by non-thermal plasma air purifiers Energy and Buildings. 2016, 130, 238-43

This work was supported by the Funded by Bureau of Culture and Tourism of Fangshan District, Beijing (The research on improving the flavour quality of Fangshan Wine).

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2024 Editorial Office of Food Innovation and Advances